CN103214347A - Method for producing cyclohexanol through benzene - Google Patents
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- CN103214347A CN103214347A CN2013101354403A CN201310135440A CN103214347A CN 103214347 A CN103214347 A CN 103214347A CN 2013101354403 A CN2013101354403 A CN 2013101354403A CN 201310135440 A CN201310135440 A CN 201310135440A CN 103214347 A CN103214347 A CN 103214347A
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Abstract
The invention provides a method for producing cyclohexanol through benzene. The method comprises the following steps of: (1) hydrogenation reaction; (2) esterification reaction; (3) separation of esterification products; (4) dehydrogenation reaction; (5) hydrolysis reaction; and (6) separation of hydrolysate. According to the method, the process of producing the cyclohexanol through the benzene is realized, generation of cyclohexane is avoided, the extracting, rectifying and separating processes of benzene, cyclohexene and cyclohexane are saved, and the equipment investment and energy consumption in separation are obviously reduced; and the method has the advantages of being high in conversion rate of raw materials, and high in product selectivity.
Description
Technical field
The invention belongs to chemical production field, be specifically related to a kind of method of producing hexalin by benzene.
Background technology
Hexalin a kind of good in high boiling organic chemical industry's product, have a wide range of applications in the every field of Chemical Manufacture.Hexalin is mainly used in produces hexanolactam and hexanodioic acid, and then is used to produce nylon-6 and nylon-66.Hexalin also is the main raw material of the various ethenoid resin lacquers of preparation, and is used as the solvent of high molecular polymer widely, and is used to prepare softening agent, sterilant and spices etc.Therefore, hexalin has important use and market widely at aspects such as organic chemical industry's industry, coating, textile industries.
Along with the development of benzene selective hydrogen addition technology, also obtained bigger development by preparing cyclohexanol by cyclohexene hydration reaction technology.Benzene at first carries out selective hydrogenation, obtains the mixture of benzene, tetrahydrobenzene and hexanaphthene, and mixture obtains tetrahydrobenzene through three tower extracting rectifyings, and tetrahydrobenzene carries out hydration reaction and obtains hexalin then.The part but this method also comes with some shortcomings, tetrahydrobenzene obtains through extracting rectifying, and facility investment and separating energy consumption are all bigger, the operation more complicated; In addition, the chemical equilibrium constant of cyclohexene hydration reaction is 5.6 (25 ℃ time), owing to be subjected to the restriction of thermodynamic(al)equilibrium, its speed of reaction is slow, the hexalin yield is too low, goes back a small amount of methyl cyclopentene of by-product, methylcyclopentanol, dimerization hexalin and cyclohexyl ether etc. simultaneously.CN101851151A discloses a kind of method that is prepared hexalin by tetrahydrobenzene, this method is in same reactor, carboxylic acid and catalyzer exist down, earlier carry out esterification by tetrahydrobenzene and carboxylic acid at certain condition, add a certain amount of water then, the change reaction conditions is proceeded hydrolysis reaction and is prepared hexalin, but this method tetrahydrobenzene transformation efficiency is low, product is very complicated, and the later separation difficulty is bigger.
Summary of the invention
The objective of the invention is for overcoming the deficiencies in the prior art, a kind of novel method of being produced hexalin by benzene is provided.
The objective of the invention is to be achieved through the following technical solutions:
A kind of method of producing hexalin by benzene, this method comprises the steps: (1) hydrogenation reaction: benzene and hydrogen carry out selective hydrogenation in hydrogenator, hydrogenation products comprises benzene, tetrahydrobenzene and hexanaphthene; (2) esterification: hydrogenation products is under catalyst action, and tetrahydrobenzene in the hydrogenation products and acetate generation esterification generate hexalin acetate; (3) esterification products separates: the mixture of the hexalin acetate after the esterification, acetate, benzene and hexanaphthene is through fractionation by distillation, and acetate loops back esterifier; (4) dehydrogenation reaction: the benzene and the hexanaphthene that do not participate in the esterification reacting pass through dehydrogenation reactor, loop back the benzene hydrogenation device then; (5) hydrolysis reaction: hexalin acetate generates hexalin and acetate through hydrolysis reaction in the presence of catalyzer and water; (6) hydrolysate separates: the acetate behind the hydrolysis reaction, hexalin, water and ethyl cyclohexyl ester mixture are through fractionation by distillation, and acetate loops back esterifier, and hexalin acetate loops back the hydrolysis reactor.
Described method of producing hexalin by benzene, wherein, the accessory separating step comprises the separation and purification of hexalin behind the separation and purification of hexalin acetate after the esterification and the hydrolysis reaction, these accessory separation can adopt conventional water distilling apparatus to meet the demands, and its operating parameters all can be with reference to similar processing parameter control.Therefore, there is no particular limitation to described separation and purification condition among the present invention.
According to the inventive method, described hydrogenation reaction, promptly under catalyzer and reaction conditions, benzene contacts in hydrogenator with hydrogen, and hydrogenation products is the mixture of benzene, tetrahydrobenzene and hexanaphthene.Noble metal catalyst is adopted in this reaction, carries out in the presence of reaction modifier, and reactor and reactive mode can adopt still formula continuous hydrogenation reaction process, also can adopt tubular type continuous hydrogenation reaction process.
According to the inventive method, benzene hydrogenation preferably adopts still formula process for selective hydrogenation, under hydrogenation catalyst and properties-correcting agent effect, and reaction pressure 3-8MPa, temperature of reaction 130-170 ℃, reacting slurry and benzene input material volume ratio 1-5:1 carry out hydrogenation reaction under the condition of stir speed (S.S.) 600-1200 rev/min and residence time 5-40 minute, and hydrogenation products is the mixture of benzene, tetrahydrobenzene and hexanaphthene.
The method of hydrotreating according to the present invention, described reacting slurry are the mixture of hydrogenation catalyst, properties-correcting agent and water, and wherein, the hydrogenation catalyst agent content is 0.2-1.8 quality %, modifier content 10-30 quality % in the reacting slurry.
The method of hydrotreating according to the present invention, described hydrogenation catalyst comprise active ingredient element and adjuvant component element, and the active ingredient element is Ru; The adjuvant component element is one or more among Zn, Fe, La, Ce, the Co.Wherein, the mol ratio of adjuvant component element and active ingredient element is 1:1-15, adopts conventional intermediate processing preparation.
The method of hydrotreating according to the present invention, described properties-correcting agent are ZnSO
4, FeSO
4, CoSO
4In one or more.
According to the inventive method, described esterification, promptly hydrogenation products contacts in esterifier with acetate under catalyzer and reaction conditions, and tetrahydrobenzene in the hydrogenation products and acetate generation esterification generate hexalin acetate.This reaction can be adopted successive reaction, and as the catalytic distillation reactor, catalyzer adopts solid acid, as storng-acid cation exchange resin, solid super-strong acid, heteropolyacid or molecular sieve etc.This reaction also can be adopted rhythmic reaction, and as tank reactor, catalyzer can adopt liquid acid, as sulfuric acid, ionic liquid etc., also can adopt solid acid, as storng-acid cation exchange resin, solid super-strong acid, heteropolyacid or molecular sieve etc.According to esterifying reaction method of the present invention, the esterification of described hydrogenation products and acetate can be implemented according to the olefin(e) acid esterification condition of routine.At the inventive method, the esterification of hydrogenation products and acetate is preferably carried out in the catalytic distillation reactor, and catalyzer is a solid acid catalyst.
Described catalytic distillation reactor comprises a tower still, a stripping section, a conversion zone, a rectifying section and a trim the top of column condenser, filling solid acid catalyst in the conversion zone, hydrogenation products and acetate counter current contact on catalyzer, its operational condition is: tower top pressure 0.2-0.9MPa, tower top temperature 50-90 ℃, 80-120 ℃ of conversion zone middle part temperature, 120-180 ℃ of tower still temperature, reflux ratio 0.2-8.0, the mol ratio of the tetrahydrobenzene in acetate and the hydrogenation mix products is 2-8, and the acetic acid feed air speed is 0.2-10h
-1
The preferred storng-acid cation exchange resin of described solid acid catalyst, resin catalyst need to carry out pre-treatment according to means known in the art before use.
According to the inventive method, described dehydrogenation reaction, promptly under catalyzer and reaction conditions, the benzene and the hexanaphthene that do not participate in the esterification reacting carry out dehydrogenation reaction through fixed-bed reactor together, and unreacted benzene loops back the benzene hydrogenation device with the benzene that cyclohexane dehydrogenation generates.This reaction can be adopted platinum catalyst, also can adopt nickel catalyzator, perhaps both improvement catalyzer.
At the inventive method, the dehydrogenation reaction of the mixture of hexanaphthene and benzene adopts loaded platinum catalyst, and Pt content is 0.1-0.8 quality %, and carrier is Al
2O
3, SiO
2, ZrO
2, TiO
2In one or more.The mixture of hexanaphthene and benzene can also can be used gas dilution without gas dilution, as hydrogen, nitrogen, argon gas etc.
Dehydrogenation reaction method according to the present invention, the dehydrogenation reaction of the mixture of hexanaphthene and benzene can be implemented according to the dehydrogenation reaction conditions of routine, and therefore, there is no particular limitation to described dehydrogenation reaction conditions among the present invention.Generally, described dehydrogenation reaction conditions can comprise: temperature of reaction is 360-480 ℃, reaction pressure 0.1-3.0MPa, and air speed is 1-10h
-1
At the inventive method, the dehydrogenation reaction conditions of the mixture of hexanaphthene and benzene is: temperature of reaction is 380-460 ℃, reaction pressure 0.3-1MPa, and in hexanaphthene, air speed 3-9h
-1Dehydrogenation feed is preferably used diluted in hydrogen, and hydrogen and raw material (mixture of hexanaphthene and benzene) volume ratio is 100-10000.
According to the inventive method, described hydrolysis reaction, promptly under catalyzer and reaction conditions, hexalin acetate contacts with water, and the hexalin acetate hydrolysis generates hexalin and acetate.This reaction can be adopted rhythmic reaction, as the high pressure stirring tank, also can adopt successive reaction, as the catalytic distillation reactor, catalyzer can adopt liquid acid, as sulfuric acid, ionic liquid etc., also can adopt solid acid, as storng-acid cation exchange resin, solid super-strong acid, heteropolyacid or molecular sieve etc.Hydrolysate obtains the hexalin product after separating, acetate then loops back esterifier and continues reaction.
Hydrolysis reaction method according to the present invention, the hydrolysis reaction of hexalin acetate and water can be implemented according to the hydrolysis reaction condition of routine.Therefore, there is no particular limitation to described ester hydrolysis reaction condition among the present invention.Generally, described ester hydrolysis reaction condition can comprise: temperature of reaction is 120-180 ℃, and the reaction times is 2-10 hour, and catalyst levels is 0.5-10 quality %.At the inventive method, described hydrolysis reaction preferably carries out in the catalytic distillation reactor.The catalytic distillation reactor comprises the conversion zone of a tower still and reboiler, one or more indirect arrangements and rectifying section, a trim the top of column condenser, filling solid acid catalyst in the conversion zone, its operational condition is: tower top pressure 0.3-1.2MPa, tower top temperature 50-90 ℃, 100-150 ℃ of conversion zone middle part temperature, 140-240 ℃ of tower still temperature, water and hexalin acetate mol ratio are 2-8, ester charging air speed is 0.2-4h
-1
Preferred storng-acid cation exchange resin of described solid acid catalyst or heteropolyacid catalyst need to carry out pre-treatment according to means known in the art before use.
Compare with existing method, the inventive method can utilize benzene to produce hexalin to greatest extent, avoid the production of low value-added hexanaphthene, omitted the extracting rectifying sepn process of benzene, tetrahydrobenzene and hexanaphthene simultaneously, significantly reduced facility investment and separating energy consumption.In addition, the inventive method has the high and high advantage of selectivity of product of feed stock conversion.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
Technical process below by way of embodiments and drawings is elaborated to the specific embodiment of the present invention and implementation result.Should be understood that, for those of ordinary skills, can be improved according to the above description or conversion, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Embodiment 1-5 is the preparing cyclohexene from benzene added with hydrogen reaction.
Embodiment 1
In tank reactor, carry out the preparing cyclohexene from benzene added with hydrogen reaction, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 2:1, catalyst content is 0.7 quality % (the Co/Ru mol ratio is 1:9) in the reacting slurry, ZnSO
4Concentration is 21 quality %.Hydrogenation conditions is: reaction pressure 6MPa, 137 ℃ of temperature of reaction, 1000 rev/mins of stir speed (S.S.)s and 14 minutes residence time, the hydrogenation products successive enters the product surge tank from the high-pressure hydrogenation still, and it is to contain the oil phase of benzene, tetrahydrobenzene, hexanaphthene and contain catalyzer and ZnSO
4Water, after oily water separation, contain catalyzer, ZnSO
4Loop back high-pressure hydrogenation still continuation participation reaction with the reacting slurry of water, benzene, tetrahydrobenzene and hexanaphthene enter the product jar.Wherein benzene accounts for 55 quality %, and tetrahydrobenzene accounts for 37 quality %, and all the other are hexanaphthene.
Embodiment 2
In tank reactor, carry out the preparing cyclohexene from benzene added with hydrogen reaction, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 5:1, catalyst content is 0.2 quality % (the Zn/Ru mol ratio is 1:1) in the reacting slurry, ZnSO
4Concentration is 10 quality %.Hydrogenation conditions is: reaction pressure 8MPa, 170 ℃ of temperature of reaction, 1200 rev/mins of stir speed (S.S.)s and 5 minutes residence time, the hydrogenation products successive enters the product surge tank from the high-pressure hydrogenation still, and it is to contain the oil phase of benzene, tetrahydrobenzene, hexanaphthene and contain catalyzer and ZnSO
4Water, after oily water separation, contain catalyzer, ZnSO
4Loop back high-pressure hydrogenation still continuation participation reaction with the reacting slurry of water, benzene, tetrahydrobenzene and hexanaphthene enter the product jar.Wherein benzene accounts for 60 quality %, and tetrahydrobenzene accounts for 33 quality %, and all the other are hexanaphthene.
Embodiment 3
In tank reactor, carry out the preparing cyclohexene from benzene added with hydrogen reaction, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 1:1, catalyst content is 1.8 quality % (the Fe/Ru mol ratio is 1:15) in the reacting slurry, FeSO
4Concentration is 30 quality %.Hydrogenation conditions is: reaction pressure 3MPa, 130 ℃ of temperature of reaction, 600 rev/mins of stir speed (S.S.)s and 30 minutes residence time, the hydrogenation products successive enters the product surge tank from the high-pressure hydrogenation still, and it is to contain the oil phase of benzene, tetrahydrobenzene, hexanaphthene and contain catalyzer and FeSO
4Water, after oily water separation, contain catalyzer, FeSO
4Loop back high-pressure hydrogenation still continuation participation reaction with the reacting slurry of water, benzene, tetrahydrobenzene and hexanaphthene enter the product jar.Wherein benzene accounts for 34 quality %, and tetrahydrobenzene accounts for 50 quality %, and all the other are hexanaphthene.
Embodiment 4
In tank reactor, carry out the preparing cyclohexene from benzene added with hydrogen reaction, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 3:1, catalyst content is 0.5 quality % (the Ce/Ru mol ratio is 1:12) in the reacting slurry, CoSO
4Concentration is 23 quality %.Hydrogenation conditions is: reaction pressure 5.3MPa, 130 ℃ of temperature of reaction, 900 rev/mins of stir speed (S.S.)s and 40 minutes residence time, the hydrogenation products successive enters the product surge tank from the high-pressure hydrogenation still, and it is to contain the oil phase of benzene, tetrahydrobenzene, hexanaphthene and contain catalyzer and CoSO
4Water, after oily water separation, contain catalyzer, CoSO
4Loop back high-pressure hydrogenation still continuation participation reaction with the reacting slurry of water, benzene, tetrahydrobenzene and hexanaphthene enter the product jar.Wherein benzene accounts for 42 quality %, and tetrahydrobenzene accounts for 49 quality %, and all the other are hexanaphthene.
Embodiment 5
In tank reactor, carry out the preparing cyclohexene from benzene added with hydrogen reaction, reacting slurry and benzene enter autoclave continuously, and wherein, the volumetric flow rate ratio of reacting slurry and benzene is 2:1, catalyst content is 0.9 quality % (the La/Ru mol ratio is 1:7) in the reacting slurry, CoSO
4Concentration is 12 quality %.Hydrogenation conditions is: reaction pressure 7.1MPa, 153 ℃ of temperature of reaction, 1100 rev/mins of stir speed (S.S.)s and 8 minutes residence time, the hydrogenation products successive enters the product surge tank from the high-pressure hydrogenation still, and it is to contain the oil phase of benzene, tetrahydrobenzene, hexanaphthene and contain catalyzer and CoSO
4Water, after oily water separation, contain catalyzer, CoSO
4Loop back high-pressure hydrogenation still continuation participation reaction with the reacting slurry of water, benzene, tetrahydrobenzene and hexanaphthene enter the product jar.Wherein benzene accounts for 63 quality %, and tetrahydrobenzene accounts for 33 quality %, and all the other are hexanaphthene.
Embodiment 6-9
Embodiment 6-9 is the esterification of acetate and hydrogenation products (benzene, tetrahydrobenzene and hexanaphthene).In catalytic distillation tower, hydrogenation products contacts on different solid acid catalyst surfaces respectively with acetate, and through the catalytic esterification Synthesis of Cyclohexyl Acetate, concrete outcome sees Table 1.
Table 1Acetate and tetrahydrobenzene catalytic distillation Synthesis of Cyclohexyl Acetate
Embodiment 10-13
Embodiment 10-13 is the fixed-bed dehydrogenation reaction of benzene and hexanaphthene mixture, and the mixture of benzene and hexanaphthene is a dehydrogenation feed.Wherein, air speed is in the hexanaphthene in the mixture, and hydrogen to oil volume ratio is the radiometer with hydrogen and volume of mixture.Reaction conditions and the results are shown in Table 2.
Table 2The mixture dehydrogenation reaction result of benzene and hexanaphthene
Embodiment 14-17
Embodiment 14-17 is that the hydrolysis reaction of hexalin acetate prepares hexalin, and reaction result sees Table 3.
Table 3Hexalin acetate is the hydrolysis synthesizing cyclohexanol in the catalytic distillation reactor
Claims (9)
1. method of producing hexalin by benzene, it is characterized in that: comprise the steps: (1) hydrogenation reaction: benzene and hydrogen carry out selective hydrogenation in hydrogenator, hydrogenation products comprises benzene, tetrahydrobenzene and hexanaphthene; (2) esterification: hydrogenation products is under catalyst action, and tetrahydrobenzene in the hydrogenation products and acetate generation esterification generate hexalin acetate; (3) esterification products separates: the mixture of the hexalin acetate after the esterification, acetate, benzene and hexanaphthene is through fractionation by distillation, and acetate loops back esterifier; (4) dehydrogenation reaction: the benzene and the hexanaphthene that do not participate in the esterification reacting pass through dehydrogenation reactor, loop back the benzene hydrogenation device then; (5) hydrolysis reaction: hexalin acetate generates hexalin and acetate through hydrolysis reaction in the presence of catalyzer and water; (6) hydrolysate separates: the acetate behind the hydrolysis reaction, hexalin, water and ethyl cyclohexyl ester mixture are through fractionation by distillation, and acetate loops back esterifier, and hexalin acetate loops back the hydrolysis reactor.
2. method according to claim 1, it is characterized in that: described benzene hydrogenation adopts still formula continuous hydrogenation mode, and reaction conditions is: reaction pressure 3-8MPa, temperature of reaction 130-170 ℃, reacting slurry and benzene input material volume ratio 1-5:1, stir speed (S.S.) 600-1200 rev/min and benzene in reactor residence time 5-40 minute.
3. method according to claim 2 is characterized in that: described reacting slurry is the mixture of hydrogenation catalyst, properties-correcting agent and water, and wherein, the hydrogenation catalyst agent content is 0.2-1.8 quality %, modifier content 10-30 quality %, and properties-correcting agent is ZnSO
4, FeSO
4, CoSO
4In one or more.
4. method according to claim 3, it is characterized in that: the active ingredient element of described hydrogenation catalyst is Ru, the adjuvant component element is one or more among Zn, Fe, La, Ce, the Co, and wherein, the mol ratio of adjuvant component element and active ingredient element is 1:1-15.
5. method according to claim 1 is characterized in that: described esterification adopts successive reaction, preferably carries out in the catalytic distillation reactor, and catalyzer adopts solid acid, preferred storng-acid cation exchange resin.
6. method according to claim 5, it is characterized in that: described catalytic distillation reactor comprises a tower still, a stripping section, a conversion zone, a rectifying section and a trim the top of column condenser, loading catalyst in the conversion zone, its operational condition is: tower top pressure 0.2-0.9MPa, tower top temperature 50-90 ℃, 80-120 ℃ of conversion zone middle part temperature, 120-180 ℃ of tower still temperature, reflux ratio 0.2-8.0, the mol ratio of the tetrahydrobenzene in acetate and the hydrogenation mix products is 2-8, and the acetic acid feed air speed is 0.2-10h
-1
7. method according to claim 1 is characterized in that: described dehydrogenation reaction adopts loaded platinum catalyst, and Pt content is 0.1-0.8 quality %, and carrier is Al
2O
3, SiO
2, ZrO
2, TiO
2In one or more.
8. method according to claim 7 is characterized in that: described dehydrogenation reaction conditions is: temperature of reaction is 380-460 ℃, reaction pressure 0.3-1MPa, and in hexanaphthene, air speed 3-9h
-1, the volume ratio of carrier gas and mixing raw material is 100-10000.
9. method according to claim 1, it is characterized in that: described ethyl cyclohexyl ester hydrolysis reaction carries out in the catalytic distillation reactor, the catalytic distillation reactor comprises the conversion zone of a tower still and reboiler, one or more indirect arrangements and rectifying section, a trim the top of column condenser, filling solid acid catalyst in the conversion zone, its operational condition is: tower top pressure 0.3-1.2MPa, tower top temperature 50-90 ℃, 100-150 ℃ of conversion zone middle part temperature, 140-240 ℃ of tower still temperature, water and hexalin acetate mol ratio are 2-8, and ester charging air speed is 0.2-4h
-1
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108069819A (en) * | 2016-11-11 | 2018-05-25 | 中国石油化工股份有限公司抚顺石油化工研究院 | A kind of method for preparing cyclopentanol |
| CN111548267A (en) * | 2020-06-19 | 2020-08-18 | 凯瑞环保科技股份有限公司 | Process device and process method for preparing cyclopentanol from cyclopentene |
| CN111559955A (en) * | 2020-06-19 | 2020-08-21 | 凯瑞环保科技股份有限公司 | Device and method for synthesizing cyclohexanol from cyclohexene |
| CN111559958A (en) * | 2020-06-19 | 2020-08-21 | 凯瑞环保科技股份有限公司 | Process device and process method for preparing cyclohexanol from cyclohexene |
| CN111606780A (en) * | 2020-06-19 | 2020-09-01 | 凯瑞环保科技股份有限公司 | Device and method for synthesizing cyclopentanol from cyclopentene |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108069819A (en) * | 2016-11-11 | 2018-05-25 | 中国石油化工股份有限公司抚顺石油化工研究院 | A kind of method for preparing cyclopentanol |
| CN108069819B (en) * | 2016-11-11 | 2020-10-27 | 中国石油化工股份有限公司抚顺石油化工研究院 | Method for preparing cyclopentanol |
| CN111548267A (en) * | 2020-06-19 | 2020-08-18 | 凯瑞环保科技股份有限公司 | Process device and process method for preparing cyclopentanol from cyclopentene |
| CN111559955A (en) * | 2020-06-19 | 2020-08-21 | 凯瑞环保科技股份有限公司 | Device and method for synthesizing cyclohexanol from cyclohexene |
| CN111559958A (en) * | 2020-06-19 | 2020-08-21 | 凯瑞环保科技股份有限公司 | Process device and process method for preparing cyclohexanol from cyclohexene |
| CN111606780A (en) * | 2020-06-19 | 2020-09-01 | 凯瑞环保科技股份有限公司 | Device and method for synthesizing cyclopentanol from cyclopentene |
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Application publication date: 20130724 |